Methanesulfonamide → HCID 68605338, compound

HRID 218073Notes

Reaction equation

HRID 218073 reaction equation
[OH:1][C@@H:2]([CH2:22][CH2:23][CH2:24][CH2:25][CH3:26])[CH2:3][CH2:4][C@@H:5]([O:14][CH2:15][CH:16]1[CH2:20][CH2:19][C:18](=[O:21])[NH:17]1)[C:6]1[S:10][C:9]([C:11](O)=[O:12])=[CH:8][CH:7]=1.Cl.CN(C)CCCN=C=NCC.[CH3:39][S:40]([NH2:43])(=[O:42])=[O:41]>CN(C)C1C=CN=CC=1.CN(C=O)C.CCOC(C)=O>[OH:1][C@@H:2]([CH2:22][CH2:23][CH2:24][CH2:25][CH3:26])[CH2:3][CH2:4][C@@H:5]([O:14][CH2:15][CH:16]1[CH2:20][CH2:19][C:18](=[O:21])[NH:17]1)[C:6]1[S:10][C:9]([C:11]([NH:43][S:40]([CH3:39])(=[O:42])=[O:41])=[O:12])=[CH:8][CH:7]=1

Participants

7

Reactant 3

HCID 72879MethanesulfonamideHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 68608006HCID 68608006, compound

Product 1

HCID 68605338HCID 68605338, compoundYield 25%

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

Acid 6 (12 mg, 0.031 mmol), 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (EDCI, 8.4 mg, 0.044 mmol), 4-dimethylaminopyridine (DMAP, 4.6 mg, 0.038 mmol) and methanesulfonamide (9 mg, 0.095 mmol) were dissolved in DMF (0.2 mL) and the resulting solution was stirred at room temperature under an atmosphere of nitrogen. After 15 h the solution was diluted with EtOAc (20 mL) and washed with 1N aqueous HCl (3×5 mL) and brine (5 mL), then dried (Na2SO4), filtered and concentrated in vacuo. Purification of the crude residue by flash column chromatography on 4 g of silica gel (CH2Cl2→10% MeOH/CH2Cl2, gradient) afforded 3.5 mg (25%) of the title compound (7).

Workup

  1. washwashed with 1N aqueous HCl (3×5 mL) and brine (5 mL)
  2. dry with materialdried (Na2SO4)
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customPurification of the crude residue by flash column chromatography on 4 g of silica gel (CH2Cl2→10% MeOH/CH2Cl2, gradient)

Sources & evidence

ORD record
ord-03c6fea7f01f481b99e8fecb6a85b3f2
Source dataset
uspto-grants-2012_06
Patent number
US08198315B2

Reaction notes

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